CN100391428C - Preparation of light curing composite resin material in oral cavity - Google Patents
Preparation of light curing composite resin material in oral cavity Download PDFInfo
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- CN100391428C CN100391428C CNB2005100165611A CN200510016561A CN100391428C CN 100391428 C CN100391428 C CN 100391428C CN B2005100165611 A CNB2005100165611 A CN B2005100165611A CN 200510016561 A CN200510016561 A CN 200510016561A CN 100391428 C CN100391428 C CN 100391428C
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Abstract
The present invention relates to a light curing composite resin for oral cavities, which comprises resins and stuffing. The resins are prepared from 2.5 to 20 wt% of super cladodification polyester-HPIP-A, 20 to 50 wt % of bisphenol A dimethyl acrylic acid glycidyl ester (BisGMA), 35 to 60 wt% of dimethyl acrylic acid diglycidyl triethylene glycol ester (TEGDMA), 0.25 to 2.5 wt% of camphorquinone (CQ) used as an initiator and 0.25 to 2.5 wt% of N, N-dimethyl ethyl acrylate (DMAEMA) used as a coinitiator. The stuffing is powdered glass 8235 made by a Schott company (Germany), and the weight of the stuffing accounts for 65 to 80 % of the total weight of the composite resins. In the preparation method, the HPIP-A, the BisGMA and the TEGDMA are uniformly stirred and mixed in a water bath at the temperature of 45 to 55 DEG C, and the CQ and the DMAEMA are added to be uniformly mixed; then, the mixture is filled into a brown bottle to be placed at the temperature of 4 to 10 DEG C in darkness for more than 24 hours, and the CQ is dissolved sufficiently. 20 to 35 wt% of resin is added to 65 to 80 wt% of Schott powdered glass 8235 to be uniformly mixed, and the mixture is put into a vacuum drying oven for 12 to 24 hours to remove gas bubbles. Thus, the composite resins for oral cavities are obtained.
Description
Technical field
The present invention relates to a kind of novel light-cured composite resin for oral cavity preparation methods.
Background technology
The oral cavity composite resin be last century middle nineteen sixties as back dental restoration material and occurring.In the last few years, the composite resin development was very fast, and it is used also more and more widely.
Composite resin is mainly combined by organic resin substrate and inorganic filler and forms, general main four parts that comprise: (1) organic substrate, organic substrate are prolonged the stabilizing agent of composite resin storage life etc. in addition and form by polymerisable monomer system, the light initiation system that can cause Raolical polymerizable; (2) inorganic filler is generally glass dust, silica flour or aerosil etc.; (3) coupling agent is generally organo-silicon compound, can be connected together organic substrate and inorganic filler with chemical bond-linking; (4) light initiation system causes Raolical polymerizable.
Although above each component is all influential to the last performance of composite resin, influence the organic substrate that is mainly of composite resin mechanical performance and micro.Therefore scientist has carried out a large amount of research at the monomer and the oligomer of composite resin organic substrate in the last few years.
Bisphenol-A methacrylate ethylene oxidic ester (BisGMA) is the composite resin monomer that occurs the earliest, also be most widely used monomer.The composite resin that occurs on many markets all is principal monomer with BisGMA, and also shows superior performance clinically.And BisGMA also has a lot of deficiencies, mainly shows: (1) is suction easily, and suction causes the composite resin mechanical performance to reduce, and reduces the life-span of composite resin; (2) double bond conversion rate is not high, and mechanical strength and conversion ratio have certain related, and in general high mechanical properties is big more more for conversion ratio, and the raising of conversion ratio can reduce the leakage of unconverted monomer; (3) polymerization shrinkage is higher, and polymerization shrinkage can cause forming edge crack between composite resin and the tooth body, and finally causes forming marginal microleakage; (4) viscosity is too high, and the amount that causes adding filler is influenced, has influenced the mechanical performance of composite resin accordingly.
In the past few decades, at composite resin monomer and the research of oligomer mainly contain the following aspects: (1) BisGMA class material; (2) has the double methyl methacrylate class material of higher molecular weight and rigid structure; (3) carbamate double methyl methacrylate (UDMA); (4) spiral shell-ortho acid esters monomer etc.These materials can improve the performance of composite resin in some aspects, but the monomer that improves the composite resin overall performance is seldom arranged.
Many methyl acrylic esters material is considered to reduce the resin system micro and improves one of optimisation substance of mechanical strength in these a few class materials.But along with the increase of resin Composition molecular weight, viscosity also increases a lot, influences the addition of filler, has influenced the overall performance of composite resin accordingly.
The composite resin of U.S. Dentsply company, 3M company and Liechtenstein Ivoclar Viadent company, Main Ingredients and Appearance mostly contains BisGMA, and for example: the composite resin Main Ingredients and Appearance of the Tetric Flow of Ivoclar Viadent is BisGMA, UDMA, TEGDMA, inorganic filler; The composite resin Main Ingredients and Appearance of the Filtek P60 of 3M is BisGMA, BisEMA, UDMA, inorganic filler.The major defect of these composite resins is that conversion ratio is low, polymerization shrinkage is big.
Summary of the invention
The object of the present invention is to provide a kind of novel light-cured composite resin for oral cavity preparation methods.
Recently along with the development of polymer chemistry, a class novel high polymer-super cladodification polymer occurred, super cladodification polymer has than with the low viscosity of the linear polymer of molecular weight, and oral cavity composite resin material is needed just for this.There are some researches show that in addition aromatics and fats super branched polyester can reduce micro.
The present invention uses a kind of monomer of a kind of novel super branched polyester as the oral cavity composite resin, and the result shows that it not only can improve conversion ratio, reduce micro and also have considerable mechanical strength.
Raw material of the present invention is: (1) super branched polyester-HPIP-A accounts for the resin composition
The 2.5-20% of weight, its structure is:
(2) bisphenol-A methacrylate ethylene oxidic ester (BisGMA) accounts for the 20-50% of resin composition weight;
(3) double methyl methacrylate triethylene glycol ester (TEGDMA) accounts for the 35-60% of resin composition weight;
(4) light trigger camphorquinone (CQ) accounts for the 0.25-2.5% of resin composition weight;
(5) coinitiator N, N-dimethyl ethyl (DMAEMA) accounts for the 0.25-2.5% of resin composition weight;
(6) glass dust 8235 of Schott company (Germany) is adopted in inorganic filler, accounts for the 65-80% of composite resin gross weight;
Preparation method:
Get HPIP-A, BisGMA, TEGDMA, 45-55 ℃ of stirred in water bath, mix homogeneously adds initiator and coinitiator, stirs, and puts into brown bottle.Being placed under 4-10 ℃ more than the dark 24h of place, CQ is fully dissolved resulting resin Composition.
Get the resin of percetage by weight 20-35%, add the Schott glass dust 8235 of percetage by weight 65-80%.Put into vacuum drying oven 12-24h behind the mix homogeneously and remove bubble.So just obtained the oral cavity composite resin.
The character of estimating:
1, mechanical performance:
(1) compressive strength
The diameter that the composite resin material for preparing is put into down microscope slide is in the mould of compressive strength of 4mm, high 6mm.Another microscope slide is placed on die tip, and steps up gently, excess stock is overflowed with clip.
The center of light source window registration coupon position.Irradiation 40s, then, to sample another side irradiation 40s.Sample is put into 37 ℃ of waters bath with thermostatic control together with mould soak 15min, from mould, take out sample then and be placed in 37 ℃ of distilled water.Test after placing 23h 45min.
During test, sample is placed on the loading platform, carries out loading,, note maximum loading value until sample breakage with the speed of 1mm/min.5 samples of each sample making.
(2) flexural strength
The composite resin material for preparing is put into down in the mould of 25mm * 2mm * 2mm flexural strength of microscope slide.Another microscope slide is placed on die tip, and steps up gently, excess stock is overflowed with clip.
The center of light source window registration coupon position.Irradiation 40s, the center of another section of mobile light source window registration coupon, and partly and last time the illumination part was overlapping to some extent need to make each illumination.The irradiation 40s, until the sample various piece all illuminated the enough time.Then, aim at the sample another side and carry out same operation.Sample is put into 37 ℃ of waters bath with thermostatic control together with mould soak 15min, from mould, take out sample then and be placed in 37 ℃ of distilled water.Test after placing 23h45min.
During test, sample is placed on the loading platform, carries out loading,, note maximum loading value until sample breakage with the speed of 0.5mm/min.5 samples of each sample making.
2, polymerization shrinkage:
Polymerization shrinkage by measure before the resin components cure and solidify after density contrast obtain.The following Equation for Calculating of volume contraction:
Shrinkage factor %=(d
Before the polymerization/ d
After the polymerization-1) * 100%
Density behind monomer and the resin polymerization is all used pycnometric determination.5 samples of each sample making.
3, double bond conversion rate:
The C=C double bond conversion rate is measured with the Vertex 70 FT-IR spectrogrphs of BRUKER company, and the resin Composition before solidifying adopts the mode of filming to measure, and the resin Composition after the curing adopts the ATR pattern to measure.Each sample in measurement 3 times.
With C=O at 1720cm
-1The peak as interior mark.Conversion ratio calculates by following equation:
DC=1-[A (C=C)/A (C=O)]
Before the polymerization/ [[A (C=C)/A (C=O)]
After the polymerization
The specific embodiment
Embodiment 1:
The composition of resin part and the percetage by weight of each component:
Component weight percentage (%)
HPIP-A 5％
BisGMA 44.5％
TEGDMA 49％
CQ 0.5％
DMAEMA 1％
Preparation method: with HPIP-A, BisGMA, TEGDMA, 45 ℃ of stirred in water bath, mix homogeneously adds CQ and DMAEMA, stirs, and puts into brown bottle, is placed on the dark 24h of place under 4 ℃, and CQ is fully dissolved.
Get the resin Composition of percetage by weight 30%, add the Schott glass dust 8235 of percetage by weight 70%.Put into vacuum drying oven behind the mix homogeneously and removed bubble in 12 hours.So just obtained the oral cavity composite resin.
Mechanical performance:
Measure its intensity according to the method for measuring compressive strength and flexural strength then.
Polymerization shrinkage:
Above resin Composition is first under the situation that does not add CQ and DMAEMA, measure its density with density bottle.And then add CQ and DMAEMA, after 40 seconds, measure its density with photo solidification machine.
Then by its polymerization shrinkage of following Equation for Calculating:
Shrinkage factor %=(d
Before the polymerization/ d
After the polymerization-1) * 100%
Double bond conversion rate:
Above resin Composition is first under the situation that does not add CQ and DMAEMA, with its spectrogram that arrives of FT-IR spectrogrph.And then add CQ and DMAEMA, after 40 seconds, reuse FT-IR spectrogrph obtains its spectrogram with the photo solidification machine photograph.
Calculate its conversion ratio by following equation then:
DC=1-[A (C=C)/A (C=O)]
Before the polymerization/ [[A (C=C)/A (C=O)]
After the polymerization
The results are shown in Table 1.
Embodiment 2:
The composition of resin part and the percetage by weight of each component:
Component weight percentage (%)
HPIP-A 10％
BisGMA 39.5％
TEGDMA 49％
CQ 0.5％
DMAEMA 1.0％
Preparation method: get HPIP-A, BisGMA, TEGDMA, 50 ℃ of stirred in water bath, mix homogeneously adds CQ and DMAEMA, stirs, and puts into brown bottle, is placed on the dark 36h of place under 6 ℃, and CQ is fully dissolved.
Get the resin Composition of percetage by weight 20%, add the Schott glass dust 8235 of percetage by weight 80%.Put into vacuum drying oven behind the mix homogeneously and removed bubble in 24 hours.So just obtained the oral cavity composite resin.
The measurement of various character the results are shown in Table 1 with embodiment 1.
Embodiment 3:
The composition of resin part and the percetage by weight of each component:
Component weight percentage (%)
HPIP-A 15％
BisGMA 34.5％
TEGDMA 49％
CQ 0.5％
DMAEMA 1％
Preparation method: with HPIP-A, BisGMA, TEGDMA, at 55 ℃ of stirred in water bath, mix homogeneously.Add CQ and DMAEMA, stir, put into brown bottle, under 10 ℃, be placed on the dark 48h of place, CQ is fully dissolved.
Get the resin Composition of percetage by weight 35%, add the Schott glass dust 8235 of percetage by weight 65%.Put into vacuum drying oven behind the mix homogeneously and removed bubble in 12 hours.Get the oral cavity composite resin.
The measurement of various character the results are shown in Table 1 with embodiment 1.
Comparative example 1:
The composition of resin part and the percetage by weight of each component:
Component weight percentage (%)
BisGMA 49.5％
TEGDMA 49％
CQ 0.5％
DMAEMA 1％
Preparation method: get BisGMA, TEGDMA, 45 ℃ of stirred in water bath, mix homogeneously adds CQ and DMAEMA, stirs, and puts into brown bottle, is placed on the dark 24h of place under 10 ℃, and CQ is fully dissolved.
Get the resin Composition of percetage by weight 30%, add the Schott glass dust 8235 of percetage by weight 70%.Put into vacuum drying oven behind the mix homogeneously and removed bubble in 12 hours.Get the oral cavity composite resin.
The measurement of various character the results are shown in Table 1 with embodiment 1.
Comparative example 2:
The composite resin Spectrum of Dentsply company is measured its compressive strength and flexural strength according to the method for embodiment 1, the results are shown in Table 1.
The test result of the various character of table 1, numerical value is standard deviation in the bracket.
Claims (1)
1. light-cured composite resin for oral cavity preparation methods, (1) super branched polyester-HPIP-A accounts for the 2.5-20% of resin composition weight, and its structure is:
(2) bisphenol-A methacrylate ethylene oxidic ester accounts for the 20-50% of resin composition weight;
(3) double methyl methacrylate triethylene glycol ester accounts for the 35-60% of resin composition weight;
(4) light trigger camphorquinone accounts for the 0.25-2.5% of resin composition weight;
(5) coinitiator N, the N-dimethyl ethyl accounts for the 0.25-2.5% of resin composition weight;
(6) glass dust 8235 of Schott company is adopted in inorganic filler, accounts for the 65-80% of composite resin gross weight;
Preparation method:
Get super branched polyester-HPIP-A, bisphenol-A methacrylate ethylene oxidic ester, double methyl methacrylate triethylene glycol ester, 45-55 ℃ of stirred in water bath, mix homogeneously, add light trigger and coinitiator, stir, put into brown bottle, being placed under 4-10 ℃ more than the dark 24h of place, Camphora a kind of jade is fully dissolved resulting resin Composition;
Get the resin of percetage by weight 20-35%, add the Schott glass dust 8235 of percetage by weight 65-80%, put into vacuum drying oven 12-24h behind the mix homogeneously and remove bubble, get the light-cured composite resin for oral cavity material.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100165611A CN100391428C (en) | 2005-02-01 | 2005-02-01 | Preparation of light curing composite resin material in oral cavity |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100165611A CN100391428C (en) | 2005-02-01 | 2005-02-01 | Preparation of light curing composite resin material in oral cavity |
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| CN100391428C true CN100391428C (en) | 2008-06-04 |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101244013B (en) * | 2008-03-21 | 2010-04-07 | 华南理工大学 | Nano-composite resin dental material for numerical control machine-shaping and preparation thereof |
| CN102670414A (en) * | 2012-04-10 | 2012-09-19 | 李军 | Dual-curing orthodontic treatment adhesion resin |
| CN104490609B (en) * | 2014-12-18 | 2017-07-18 | 上海纳米技术及应用国家工程研究中心有限公司 | Graphene oxide and nano silicon oxide compounded mix strengthen the preparation of gear division binding agent |
| CN105496797A (en) * | 2015-12-14 | 2016-04-20 | 天津君润新材料科技有限公司 | Photo-curable anti-caries fluoride coating film |
| CN105456039A (en) * | 2015-12-15 | 2016-04-06 | 江苏乘鹰新材料股份有限公司 | Visible light cured dental restorative composition and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1091001A (en) * | 1992-11-04 | 1994-08-24 | 英国技术集团有限公司 | The compositions of command-curable |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1091001A (en) * | 1992-11-04 | 1994-08-24 | 英国技术集团有限公司 | The compositions of command-curable |
Non-Patent Citations (1)
| Title |
|---|
| A novel hyperbranched polyisophthalate used as polymericbinders in holographic diffraction gratings. Huiguang Kou et al.Journal of photochemistry and photobiology A: chemistry,Vol.163 . 2004 * |
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